3-[(3R,4S,5R)-3-(furan-2-yl)-5-methyl-2-phenyl-1,2-oxazolidine-4-carbonyl]-1,3-oxazolidin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 3-[(3R,4S,5R)-3-(furan-2-yl)-5-methyl-2-phenyl-1,2-oxazolidine-4-carbonyl]-1,3-oxazolidin-2-one
• 化学式: C₁₈H₁₈N₂O₅
• 分子量: 342.351
• InChiKey: BBKJHIOWSKHJFE-WQVCFCJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  72.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-[(E)-2-丁酰基]-1,3-噁唑烷-2-酮 、 C-(2-furyl)-N-phenyl nitrone 在 N,N'-bis(2,6-dichlorobenzylidene)cyclohexane-1,2-diamine 、 4 A molecular sieve 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 3-[(3R,4S,5R)-3-(furan-2-yl)-5-methyl-2-phenyl-1,2-oxazolidine-4-carbonyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Catalytic highly enantioselective 1,3-dipolar cycloaddition reaction of nitrones with 3-alkenoyl-2-oxazolidinones by use of a bidentate chiral bis(imine) ligand–Cu(II) triflate complex

  摘要：

  A copper(II) triflate complex with bidentate, chiral C-2-symmetric cyclohexane-1,2-bis[(2,6-dichlorophenylmethylene)amine] catalyzed the 1,3-dipolar cycloaddition reactions of nitrones with electron-deficient dipolarophiles, 3-(2-alkenoyl)-1,3oxazolidin-2-ones to give isoxazolidine cycloadducts with extremely high endo- and en antio selectivities. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.150

文献信息

• Evaluation of chiral bidentate ligand–metal complexes in asymmetric 1,3-dipolar cycloaddition reaction of nitrones with 3-alkenoyl-2-oxazolidinones
  作者：Takao Saito、Takuya Yamada、Shingo Miyazaki、Takashi Otani

  DOI：10.1016/j.tetlet.2004.10.149

  日期：2004.12

  of a chiral C2-symmetric bis(oxazoline) ligand, its Lewis acid complexes-catalyzed asymmetric 1,3-dipolar cycloaddition reactions of nitrones with electron-deficient dipolarophiles, 3-(2-alkenoyl)-1,3-oxazolidin-2-ones, have been investigated and it was found that the cycloadditions using a Cu(II)-bis(oxazoline) complex under optimized reaction conditions induced extremely high enantioselectivity.

  为了评估手性C 2对称双（恶唑啉）配体，其路易斯酸络合物催化的硝酮与缺电子的双极性亲和剂3-（2-链烯酰基）-1,3-恶唑烷酮的不对称1,3-偶极环加成反应研究了-2-一，发现在优化的反应条件下使用Cu（II）-双（恶唑啉）配合物进行环加成反应可产生极高的对映选择性。
• Kobayashi, Shu; Akiyama, Ryo; Kawamura, Mikako, Chemistry Letters, 1997, # 10, p. 1039 - 1040
  作者：Kobayashi, Shu、Akiyama, Ryo、Kawamura, Mikako、Ishitani, Haruro

  DOI：——

  日期：——
• Catalytic highly enantioselective 1,3-dipolar cycloaddition reaction of nitrones with 3-alkenoyl-2-oxazolidinones by use of a bidentate chiral bis(imine) ligand–Cu(II) triflate complex
  作者：Takao Saito、Takuya Yamada、Shingo Miyazaki、Takashi Otani

  DOI：10.1016/j.tetlet.2004.10.150

  日期：2004.12

  A copper(II) triflate complex with bidentate, chiral C-2-symmetric cyclohexane-1,2-bis[(2,6-dichlorophenylmethylene)amine] catalyzed the 1,3-dipolar cycloaddition reactions of nitrones with electron-deficient dipolarophiles, 3-(2-alkenoyl)-1,3oxazolidin-2-ones to give isoxazolidine cycloadducts with extremely high endo- and en antio selectivities. (C) 2004 Elsevier Ltd. All rights reserved.